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- Fill in the blanks: (a) to (i): Determine whether each stereocenter marked by letters in red is R or S: H,N CI F CI SH a b SH Br Br CI 1(a). 2(b). 3(c). 4(d). 5(е). 6(f). 7(g). 8(h). 9(1).organic chemistry II please label the important peaks for me and explain why1:23 10) Match each molecule with its IR spectrum. Explain your choice by detailing (specifically addressing the location, intensity, and breadth of important peaks) the important differences in the following specific regions of the spectrum. 100 TRANSHETTANCES D 100 TRANSHE CANCES 4000 D 4000 3000 Photo 3000 2000 2000 a. The C-C stretching region b. The C-H stretching region H₂C=CH-CH=CH-CH=CH₂ HAVENUMBER "M 1500 RAVENUMBER 1500 1000 500 + Done 500 O
- 1) Indicate chemically equivalent nuclei (e.g. Ha, H³, Hc). 2) Estimate the chemical shifts on the following hydrogens. 3) Indicate the ratio of the area under the peaks 4) Indicate the Spin Spin splitting (singlet, doublet, triplet, etc) 1, 1, 2 tribromoethane Ethyl benzene Methyl isopropyl ketone Isopropyl propionateQ2: Choose the correct answer for each of the following: () 1 - In the infrared spectrum of a Compound containing a triple C-C bond, the amplitude oscillation band appears The Stretch) has at: - A) 2700 cm ¹ b) 2100 cm ¹ -1 c) 3100 cm ¹ 2- Stretching frequency of the O=C bond of a compound (3-butene-2-on) is less than the stretching frequency of a compound (2-propanone) a.) hydrogen bonding c) Vibration duplication b) Electronic effects 3- The compound o-hydroxybenzoic acid can be distinguished from the compound m-hydroxybenzoic Acid by infrared spectroscopy based on: a) OH. Group b) group curve oscillation) C-H c) group amplitude oscillation C=O2. (2) In proton NMR, hydrogens with environments which have the lowest electron density are found a) upfield c) downfield b) are unobservable d) can be anywhere in the spectrum 3. (1) How many signals (peaks) are found for the H atom on the tertiary carbon of 2-methylpropane, due to spin-spin splitting? a) 1 b) 2 c) 4 d) 8 e) 10
- 8. (8) Predict the splitting pattern for each signal in the 'H-NMR spectrum for the following molecule (singlet, doublet, triplet, quartet, pentet, sextet, etc). Enter your answer in the appropriate blank a La ee -9 (a)__blank 1 (b) (c) (d). - blank 2 blank 3 blank 4 (e)_ - (f) (g). (h) - blank 5. blank 6 blank 7 blank 8Propanoic acid and methyl ethanoate are constitutional isomers. (c) оооо (d) CH3 оооо CH₂ OH Show how to distinguish between them by IR spectroscopy. (Use the Appendix.) (a) Which IR bands would one expect for propanoic acid? propanoic acid оооо 1200-1250 cm 1375 1450 cm 1450 1475 cm 1630-1820 cm -1 1200-1250 cm 1375 1450 cm 1450-1475 cm 1630-1820 cm 1375 1450 cm -1 -1 -1 -1 1200-1250 cm (b) Which IR bands would one expect for methyl ethanoate? -1 -1 1450 1475 cm -1 -1 1630-1820 cm -1 00000000 −1 CH₂-C 0000 methyl ethanoate If the IR spectrum shows a band at 1780 cm-¹, which isomer is it? 1700-1725 cm 1735-1800 cm 2720 cm -1 2500-3300 cm 2720 cm Which IR bands are unique to, i.e. not shared between, the two sets? -1 1700 1725 cm 2500-3300 cm -1 CH3 1735-1800 cm -1 -1 -1 2720 cm -1 2500-3300 cm -1 1700-1725 cm -1 1735-1800 cm -1 -1 -1A4 Compound: C11H18O4 For 1H and 13 C:1. Specificy the chemical shifts and multiplicity2. Specify the number of hydrogens or carbon associated for each peak in 1H and 13C spectra.3. Assigned the peaks in the proposed structure.
- 6. For each of the following molecules: i) Fill in all the C-H bonds; ii) Then identify FOUR unlque stretching frequencies that will appear in the IR spectrum in the region 1600-4000 cm ; and prediet the position (cm-1), shape and intensity of each band. a) C=C-C-H ON b) CミC-C--c と- c-と-CEN c)204hw1-1 0021.pdf CCOB 124% 1. a) Consider this compound: ch -Br b) How many signals would this compound give in the 'NMR? You may group aromatic hydrogens together as one signal. cture above, label the different types of H'S as In table form, list the peaks, the number of On the st c) А, В, с, etc. hydrogens, their shifts, and the splitting you would observe in the 'NMR spectrum of this compound, for example: # of hydrogens Shift (6) -2.0 splitting singlet Label 3 etc. 23 ?S ? tvWhich of the following groups has the highest priority for assigning R-S absolute configuration? a. CH₂=CH- b. (CH3)₂CH-*c. (CH3)3C- d. CH₂CH₂- Type here to search Bl Mar... e. CH₂- 4 Zvate Windows ^) ENG ص 01:20 T-T/-1/-0 E